(3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone | 195196-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone
• 英文别名: (3S,4S)-4-hydroxy-3-phenyl-2-[(1R)-1-phenylethyl]-1,2-oxazolidin-5-one
• CAS: 195196-15-7
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: MMHFGPHUUICZOP-KCXAZCMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone 在 palladium dihydroxide 氢气 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 甲基(2S,3S)-N-boc-3-苯基异丝氨酸盐酸
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v
• 作为产物：
  描述：

  [(1R,2S)-2-phenylcyclohexyl] (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenylethyl]amino]-3-phenyl-2-triethylsilyloxypropanoate 在 氢氟酸 作用下， 以 溶剂黄146 为溶剂， 以74%的产率得到(3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v